Thank you so much for taking the time to write this, I should have already edited it, that I figured out already it was the "Say hi to Kevin' that I couldn't trigger(not even by following the mod/pdf walkthrough) but it was too late my time and had to go to sleep.
Now I am at work and can't really test it, but of the top of my head the only path I can get the extra romantic point is if I go home with Kira instead of Cece, because I always picked the flirty point at the start for the extra +Kira at the burger place. If I am right that is textbook bad game design, I do not care how insignificant that line proves to be in the long run, you do not punish the player 5 chapters down the line for a decision they do in chapter 1, especially when is not properly communicated.
(i.e. Talk about seasons in ep1, say you like winter, lose point sin chapter 4 with LI, because they prefer Summer)
Also, the best outcome should never be offered only by getting 100% of the points. You have to leave the players some wiggle room to have some flavor with their choices, lets say maximum RP at that point are 25, the best outcome options should be offered at, let's say, 21-22 RP. Maybe I am just jumping the gun and I am yet missing some aspects, so I apologize in advance to Mr. Drifty.
On the plus side I can't wait for the update, to continue my Cece playthrough, been a while since I was so invested in a character, in a game.